That’s how much it would cost to buy each of the 10 most expensive properties. A $100 million home is not even enough to crack this year’s top 10.

By Camilla McLaughlin


The Playboy Mansion

Asking prices in this uncharted terrain might seem to be simply wishful thinking or a grab for publicity, but when viewed over the span of 11 years, an undeniable progression in both list prices and sale prices is obvious.
When Ultimate Homes debuted in 2005, the most expensive home for sale in the U.S. was $75 million and the prospect of a $200 million home seemed fanciful. Yet, little more than a decade later, the $200 million listing in the U.S. is a reality, and, according to most indicators, the $200 million club is here to stay.
Last year, an opulent Beverly Hills Estate asking $195 million, a price that gave even seasoned brokers pause, flirted with the $200 million ceiling. This year, two properties at or close to this benchmark lead the list of most expensive. The Playboy Mansion in Holmby Hills is listed at $200 million while an extensive ocean-to-Intracoastal estate in Manalapan, Florida, is priced at $195 million. More than half of the top 10 are at $150 million or more, and the ante to be among the top group is in excess of $100 million.
“All you need to do is have one property sell at a stratospheric rate and it pushes the ceiling up,” explains Paul Boomsma, president, Luxury Portfolio International and COO, LeadingRE. “When you have some of these uber-wealthy families, and they’re either global dignitaries or oil money or wherever it’s coming from, as soon as they make one purchase, it kind of signals what the new mainstay is for pricing.”
Just as this issue was going to press, a recently constructed estate at 301 Carolwood Drive near Holmby Hills came on the market priced at $150 million. “We are very excited about the opportunity with the new $150 million listing from our California company,” observed Craig Hogan, vice president of luxury, Coldwell Banker Real Estate. “The interest is certainly there for the ultra-high-end. While the numbers remain few at this level, last year gave us a sign of the interest in the $100 million-plus market globally, and the U.S. was in that mix.”
This year the ultra-world and potentially softening demand in Manhattan sparked wide ranging discussions about the implications of stratospheric prices and their impact on the market overall. What is often overlooked is just how gossamer thin this slice of real estate is. The best characterization came from John Tuccillo, former chief economist for the National Association of Realtors, who used the term sui generis, which means “unique” or “of its own kind,” to describe the ultra-market. When prices begin to exceed $50 million, value is difficult to determine. Comparables, sales records, and other object measurements applied to the general market aren’t available.
When research for the first Ultimate Homes began, lists touting the most expensive didn’t exist. No one was really sure what price point would usher in the top 850 homes for sale in the U.S. Seventy-five million dollars ended up being the top price, while $7.8 million, a figure that would not even elicit a blink in a few locales today, was the bottom benchmark. Over the years, we’ve enhanced the process but still meticulously search properties all over the country. Today, you might see similar lists, but most skim the surface, cherry picking the most publicized properties. For Ultimate Homes this year, $20 million continues to be the jumping off point for the ultra-high-end.
Prices spark media interest, but the properties themselves are the stars. Each is remarkable and usually has a story all its own, even new construction. In New York, notable buildings that once made their own statement about the city are being converted into residential towers, setting new standards for urban luxury. Built as the tallest building in the world, the Woolworth Building remains a striking icon. Under the baton of French designer Thierry Despont, the top 30 floors have been reimagined into 34 condominium residences. Original architectural details have been elevated with refined cabinetry and finishes and 15-foot ceilings. Capping the building is a seven-story penthouse reportedly priced at $110 million. Also in Manhattan, according to reputable reports, a $150 million triplex penthouse is being added to the refocused former Sony Building.
This year, legendary estates, some with a provenance that goes back generations, dominate our Ultimate list. Owned by just three families in its 80-year history, Briar Patch, an 11-acre compound on Georgica Pond in East Hampton, is on the National Register of Historic Places, a first for the Ultimate top 10. Two residences, including the Georgian Revival, six-bedroom, 10,000-square-foot main house, were painstakingly restored and renovated over two-and-a-half years by the internationally renowned architect Peter Marino.
Gemini, located in Manalapan, Florida, and our second Ultimate property, was designed by architect Marion Sims Wyeth and built in the 1940s for the Lambert pharmaceutical family. Later it was the winter retreat of Loel and Gloria Guinness. In 2003, architect Edson E. Dailey completed a total transformation of the property, reconstructing and expanding the entire residence, which also was well engineered to withstand the elements. According to Premier Estate Properties — which has the listing — there is nothing like it in southeast Florida.
This year’s top property might be known as the Playboy Mansion, but it was a significant estate long before Hugh Hefner discovered it. “It’s been special since the beginning,” says Gary Gold of Hilton & Hyland in Beverly Hills, who has the listing along with Mauricio Umansky of The Agency. “Even if it wasn’t the Playboy Mansion, it still would be one of the most desirable and valuable estate sites anywhere,” he says, noting, The Wall Street Journal described its location as the best street west of the Mississippi.
Rancho San Carlos ©JIM BARTSCH

Rancho San Carlos

The original property was created by the developer of Holmby Hills, who reserved a prime location on the north course of the Beverly Hills Country Club for his own residence. The 5-acre site is one of the largest in Holmby Hills. “At the time Hef and Playboy purchased the home, it was the largest real estate transaction in Los Angeles history,” adds Gold. “Today, we hope to make the same history with the property and its sprawling acreage, neighboring the Los Angeles Country Club.”
“It’s almost shocking that you could buy such a thing. It’s like buying the White House,” Gold says. It’s not uncommon for someone viewing the property to have been a guest at one time, but viewing it as a potential purchase is entirely different. Gold says, “When they go there to look at the real estate, it’s a whole other experience. You realize how large the property is and how epic the house, and then you come across the tennis courts and the pool.” The effect of driving up the long private drive (a rarity in Holmby Hills) and arriving at the massive stone residence is, in Gold’s words, “monumental.” Few other homes in the area share this architectural style, which evokes classic East Coast Beaux-Arts. Spend some time here and you eventually find secret spots like a redwood forest, or meet the rare tropical birds. This is also one of the few properties in Los Angeles County with a zoo license.
Another once-in-a-lifetime opportunity is Rancho San Carlos, which has been in the same family for nearly 100 years. It is one of the most historic period homes still in private hands, according to Harry Kolb with Sotheby’s International Realty in Montecito, California, who is listing the property with Suzanne Perkins, also with Sotheby’s. And the amount of land, 237 acres that cascades down the foothills of Montecito and offers panoramic vistas across the valley, is considerable. Rancho San Carlos was designed in 1931 by one of the preeminent architects of that era, Reginald Johnson, and stands as one of the most significant estates in California. With more than 30 rooms, the Monterey Colonial manor house is over 25,000 square feet. Johnson made ingenious use of the natural slope and contours of the lot by placing the bedroom wings and the public spaces on different levels and connecting them with a barrel vaulted central gallery. Not all, but many, Ultimate homes have a secret space or asset tucked away. At Rancho San Carlos it is an authentic English pub accessed from a secret hallway.
Just the size of the property alone makes it significant. “It’s an enormous piece of ground where most properties in the $50 million range are anywhere from 5 to 15 acres. It has panoramic views, and it has 30 legal parcels. That is unheard of here,” shares Kolb. Views extend to the ocean and the compound includes 10 residential cottages, extensive horse facilities, and producing orchards.
Land is still the fundamental that determines value, and every home this year is sited on a piece of land in a highly desirable location that would be almost (if not) impossible to acquire today. Owlwood sits on one of the largest parcels in Holmby Hills. Ann Dashiell with Douglas Elliman Real Estate in Beverly Hills, who has the listing, compares it to having Central Park in Holmby Hills. The estate is the result of the combination of three storied properties, including the Sony and Cher estate, which set a price record decades ago. The villa, designed by noted Los Angeles architect Robert Farquhar, is surrounded by 10 acres of lawns, giant oaks, magnolias, coral trees, and Moreton’s figs.
The size of this parcel is especially appealing to foreign buyers. Families coming from overseas are looking for a compound and want to build additional homes on the property, according to Dashiell. Also appealing to foreign buyers is privacy, and Owlwood offers the ultimate for privacy with a single guard-gated entry from a privately owned street that is part of the property. Easily, like many Ultimate homes, it could be viewed as a private island.
Private islands long have been viewed as real estate’s ultimate prize. Although none of the properties in the top 10 this year are completely surrounded by water, it’s not an overstatement to say that each of our top properties — whether a penthouse surfing Central Park and the Manhattan skyline or a classic estate encircled by acres of green like Owlwood — could be viewed as an island. Two, however, are waterfront; each occupying a desired stretch of coastline. Gemini is a 15.65-acre walled compound just outside of Palm Beach in Manalapan that is a lush oasis of old Florida. Dune-fringed beachfront along the Atlantic runs 1,200 feet and another 1,300 feet spans along the Intracoastal in a place where it almost forms a natural bay. The coral-clad main residence is elegant yet invitingly informal and surprisingly livable. It is comprised of two large wings on both the ocean and Intracoastal sides connected by a unique and irreproducible 15-foot-wide passageway that begins at ground level on one side and ends in a skylit foyer on the other. The property includes a PGA-standard golf practice area, a freshwater pond that creates a bird sanctuary, a miniature golf course, and a butterfly garden with a large-scale model train. The two large guest houses each have a high level of privacy.
Farther south in Hillsboro Beach is a second waterfront estate that also runs from ocean to Intracoastal. The 4.4-acre site includes 465 feet on the ocean and 492 feet on Intracoastal, with two docks for a 200-foot yacht. Construction was completed, and the property was reintroduced this year as Le Chateau de Versailles and priced at $159 million.
In the last decade, expectations regarding what makes a home worthy of being considered Ultimate have changed, and this property showcases the seamless integration of technology with gorgeous finishes. Extensive amenities include two 200-foot docks, an ice skating rink, and the first residential IMAX theater in the world.
Views fetch top-dollar today, and the ultimate view property might be a $135 million Beverly Hills estate created for the late comedian and actor Danny Thomas. Set on 2.5 acres on a secluded promontory in the coveted Trousdale Estates enclave, it commands 360-degree views of the entire L.A. basin from downtown to the canyons. The John Aaroe Group has this listing.
With several more ultra-properties in the works, it’s quite possible next year could bring a new record high. Even more interesting would be a record-setting sale. But don’t hold your breath. Sales at this level are “usually a lengthy process because you have a limited pool of buyers,” says Joyce Rey, executive director, Coldwell Banker Previews International in Beverly Hills, whose sales have set numerous price records. “Plus, unlike most sellers, owners of these homes have the luxury of waiting for the right price.”